Naum Isaakovich Eitingon

The operation most widely associated with Eitingon is "Duck" (Утка), the removal of Leon Trotsky in Mexican exile. Sudoplatov's memoir records that Stalin personally ordered Trotsky's elimination within one year, before the outbreak of the inevitable war; Sudoplatov headed the effort overall, while Eitingon was assigned the leading role. Eitingon accepted it without hesitation, and Sudoplatov judged him the ideal figure to head the special illegal residency in the United States and Mexico, since Trotsky could be approached only through agents settled in Mexico after the Spanish war. On Eitingon's proposal the operation was code-named "Duck," the word used in the sense of disinformation.

The operation had two independent components: the "Horse" group under the Mexican artist David Alfaro Siqueiros and the "Mother" group under Caridad Mercader. Eitingon insisted on using agents who had no prior role against Trotsky. In Spain he had already selected Ramón Mercader and sent him from Barcelona to Paris in summer 1938 under the guise of a young businessman and adventurer; Mercader and his mother Caridad had committed themselves to cooperating with Soviet intelligence by 1938. The first attempt failed: on 23 May 1940 Siqueiros's group stormed the villa but fired through a closed door, and Trotsky, hiding under a bed, survived. After that failure Stalin confirmed the alternative plan, dismissing concerns about losing the anti-Trotsky network and ordering a telegram to Eitingon expressing full confidence.

Mercader chose the weapon together with Eitingon and Caridad: a knife or a small climber's ice axe, selected because they could be hidden from guards and were silent. He rejected Eitingon's plan of a raid by five gunmen and volunteered to carry out the killing alone. On 20 August 1940 Mercader struck Trotsky with the ice axe at the Coyoacán villa, and Trotsky died the next day in hospital. Eitingon and Caridad, waiting in a car near the villa, fled when the household raised the alarm, first to Cuba. Mercader was arrested under the name Frank Jackson, and his real identity remained unknown to the Mexican authorities for six years; the plan had been for him to escape unnoticed because the guards knew him well.

After Cuba, Eitingon and Caridad stayed underground for about six months, then travelled by sea to New York, where Eitingon used his contacts in the Jewish community to obtain new documents and passports. He crossed America to Los Angeles and San Francisco, re-established contact with two agents, and in February 1941 sailed for China, returning to Moscow from Shanghai by the Trans-Siberian Railway in May 1941.

The SVR's official account frames Eitingon as deputy resident and then resident of the NKVD in Spain and the "direct supervisor" of the operation to liquidate Trotsky, code-named "Duck" and ended on 20 August 1940; it also states that he was brought into the operation as one of its leaders after Stalin ordered it. Other actions attributed to Eitingon in his career, including the assassination of Zhang Zuolin, the abductions of the White generals Kutepov and Miller in France, and involvement in removing the Spanish gold reserve, are claims credited to him by Russian-language reference material and should be presented as attributed rather than certain. On his role in the September 1937 abduction of General Yevgeny Miller in Paris, English-language accounts record that Sudoplatov himself rejected Western framings as false, leaving that attribution contested.

Eitingon's most brilliant operations were two strategic radio games he directed alongside Pavel Sudoplatov as deputy head of the 4th NKVD Directorate during the German-Soviet war. Operation Monastery (1941–1944) placed agent Alexander Demyanov (codename "Heyne") inside the Abwehr, posing as an emissary of the fictitious anti-Soviet monarchist organization "Throne." After being recruited by the Germans and reinserted into the USSR, Demyanov settled in Moscow and for over two years fed carefully scripted disinformation to Gehlen's Foreign Armies East (FHO) department.

The radio game's greatest coup came in autumn 1942, when it helped draw German reserves toward the Rzhev sector. The Wehrmacht repelled Operation Mars, but in doing so left the southern flank exposed. Operation Uranus encircled and destroyed the Sixth Army at Stalingrad. For this, Sudoplatov and Eitingon received the Order of Suvorov, the only state security officers ever so honored.

After Stalingrad, Stalin personally ordered a bolder follow-up. Operation Berezino (1944–1945) was placed under Eitingon's field command, with an operational group that included Yakov Serebryansky, Willie Fischer (later known as Rudolf Abel), and Mikhail Maklyarsky. Using captured German Lieutenant-Colonel Heinrich Scherhorn as a front, the NKVD conjured the illusion of a 2,000-man German force stranded in the marshes of the Berezina River. Otto Skorzeny's commandos launched Operation Freischütz to rescue them. Between September 1944 and May 1945, the Luftwaffe flew 39 sorties, dropping 22 commandos, 13 radio sets, and 255 cargo loads. All of it fell straight into Eitingon's hands. The deception held until the final days of the war: on May 5, 1945, Berlin radioed "with a heavy heart we must cease assistance."